2-(Trimethylsilyl)ethyl 3,4-O-isopropylidene-6-O-(2-methoxyisopropyl)-β-D-galactopyranoside | 117253-14-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 2-(Trimethylsilyl)ethyl 3,4-O-isopropylidene-6-O-(2-methoxyisopropyl)-β-D-galactopyranoside
• 英文别名: (3aS,4R,6R,7R,7aR)-4-(2-methoxypropan-2-yloxymethyl)-2,2-dimethyl-6-(2-trimethylsilylethoxy)-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-ol
• CAS: 117253-14-2
• 化学式: C₁₈H₃₆O₇Si
• 分子量: 392.565
• InChiKey: FALSLPCLSRKFRC-IBEHDNSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.35
• 重原子数：
  26.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  75.61
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-(Trimethylsilyl)ethyl 3,4-O-isopropylidene-6-O-(2-methoxyisopropyl)-β-D-galactopyranoside 在 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 、 camphor-10-sulfonic acid 、 水 、 sodium hydride 、 potassium carbonate 、 溶剂黄146 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 28.0h， 生成 methyl (2-(trimethylsilyl)ethyl 2-O-benzyl-exo-3,4-O-benzylidene-β-D-galactopyranoside)uronate
  参考文献：
  名称：

  用于迭代方法合成 1 型肺炎链球菌两性离子荚膜多糖重复单元的低聚物的构建块

  摘要：

  来自 1 型肺炎链球菌 (Spt1) 的两性离子荚膜多糖提取物，质量约为 8 kDa，已显示出独特的 T 细胞激活特性。Spt1荚膜多糖的三糖重复单元的低聚物[→3)-4-NH2-α-d-QuipNAc-(1→4)-α-d-GalpA-(1→3)-α-d-GalpA- (1-]n 需要定义长度来进一步研究这种反应。描述了一种实现 Spt1 的两性离子荚膜多糖的可迭代扩展的三糖构建块的方法。关键要素包括糖基化前氧化和糖基化后氧化方法的比较使用硫糖苷供体到目标三糖，优化后糖基化氧化方法，以及将三糖转化为为迭代糖基化量身定制的构建块。

  DOI：

  10.1139/cjc-2016-0006
• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 在 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 27.0h， 生成 2-(Trimethylsilyl)ethyl 3,4-O-isopropylidene-6-O-(2-methoxyisopropyl)-β-D-galactopyranoside
  参考文献：
  名称：

  2-(Trimethylsilyl)ethyl glycosides. 3. Synthesis, anomeric deblocking, and transformation into 1,2-trans 1-O-acyl sugars

  摘要：

  DOI：

  10.1021/jo00259a006

文献信息

• Synthesis of a Pentasaccharide Epitope for the Investigation of Carbohydrate-Protein Interactions
  作者：Todd L. Lowary、Eva Eichler、David R. Bundle

  DOI：10.1021/jo00127a043

  日期：1995.11

  Pyranose residues of a polysaccharide that are not involved in the principal sugar-protein antibody combining site, filled by trisaccharide 1, cause a 50-fold reduction in intrinsic affinity. The antibody is crystallographically characterized, and the residue responsible for the lost binding energy has been identified as the terminal disaccharide Rha-->Gal of pentasaccharide 5. This disaccharide segment of 5 may avoid protein contact by adopting the ''anti'' conformer about the preceding Man-Rha glycosidic linkage. Monosaccharide thioglycoside synthons 6-9 were used in NIS-promoted glycosylations to synthesize the pentasaccharide as a glycoside that was suitable for binding and solution conformational studies. Disaccharide 29 was obtained upon the addition of rhamnose building unit 6 to the (trimethylsilyl)ethyl galactopyranoside 10 followed by protecting group manipulation. The sequential addition of 7-9 to 29 afforded the pentasaccharide derivative 35 bearing a 2-O-benzoate group suited for subsequent 1,2-trans-glycoside synthesis following its conversion to a glycosyl imidate. In order to preserve the integrity of the 3,6-dideoxyhexopyranosyl glycosidic bond during cleavage of the (trimethylsilyl)ethyl group leading to the imidate 39, it was essential to convert the benzylated pentasaccharide target 35 into its fully acylated derivative 37. Pentasaccharide 5 was obtained by transesterification of the protected glycoside 40 formed via 39. Qualitative NOE measurements suggest a predominant solution conformation for 5 that cannot be adopted in the bound state due to protein-oligosaccharide clashes at the periphery of the binding site.
• JANSSON, KARL;AHLFORS, STEFAN;FREJD, TORBJORN;KIHLBERG, JAN;MAGNUSSON, GO+, J. ORG. CHEM., 53,(1988) N 24, C. 5629-5647
  作者：JANSSON, KARL、AHLFORS, STEFAN、FREJD, TORBJORN、KIHLBERG, JAN、MAGNUSSON, GO+

  DOI：——

  日期：——